Shanghai Pharmaceutical Institute and others found new ingredients with immunosuppressive activity in Neem plants
Recently, researchers from the Shanghai Institute of Materia Medica of the Chinese Academy of Sciences have discovered a new type of macrolide (Ivorenolide A) with immunosuppressive activity from the plant of Khaya ivorensis. The compound has a rare conjugated diacetylene fragment and 5 chiral centers, and forms an 18-membered macrolide structure at the 1,17-position. The researchers determined their relative three-dimensional structure by means of spectroscopy, X-single crystal diffraction and other means, and also proposed a possible source of formation of the compound.
Inspired by the biogenic synthesis route, the researchers conducted a chiral total synthesis of the compound, and obtained its enantiomers with 12-step linear synthesis and a total yield of 22% (specific optical rotation is opposite to CD), thus confirming The absolute stereo configuration of the macrolide (ivorenolide A).
The compound and its synthesized enantiomer both showed good immunosuppressive activity and selectivity. The discovery of Ivorenolide A and its synthesized enantiomers provides a relatively simple and completely new type of lead structure for the development of new immunosuppressants. The study also found that the natural macrolide (ivorenolide A) has interesting self-assembly phenomena in both solid and solution states.
This research was carried out in collaboration with Yue Jianmin's research group, Zuo Jianping's research group, and Lanzhou University's Li Ying's research group. The research results have been published online in the Journal of the American Chemical Society. So far, Yue Jianmin's research team has achieved fruitful results in the research on the chemical composition and biological activity of neem family plants, and has completed the research on the chemical composition and biological activity of more than 30 species of this family of plants. There are more than 400 new compounds and 35 new skeleton compounds; 42 compounds with significant biological activity were found. Some research results have been published in Org. Lett. (12 articles), J. Nat. Prod. (12 articles) and other international journals, and nearly 50 articles have been published, and invited to write relevant research reviews (Chem. Rev. 2009, 109, 1092) .
The research work was supported by projects from the National Natural Science Foundation of China and the Ministry of Science and Technology.
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